Inspiration starts with connection.
Through mentorship, students gain confidence, build skills, and discover their potential.
At Dream Big Mentoring and Outreach, we believe that every child deserves consistent guidance, positive role models, and opportunities that empower them to rise above their circumstances. Our Mentoring Program provides a structured, compassionate alternative for youth who need encouragement, direction, and meaningful connection.
At Dream Big, we believe every young person deserves guidance, encouragement, and opportunity.
Mentors and staff undergo extensive training and background checks to ensure the safety and well-being of every student. We are committed to creating a positive, inclusive environment where every participant feels valued, supported, and inspired to reach their potential.
Through a network of trained mentors, educators, and social service professionals, we deliver a comprehensive range of programs that foster personal growth, academic achievement, and lifelong success.
These include:
Dream Big Life Labs reimagines mentoring by turning learning into an interactive, immersive experience where young people do instead of simply being told. Each session becomes a dynamic environment that feels more like a creative studio, innovation hub, or training lab than a traditional classroom. Youth are encouraged to explore, test ideas, take risks, and discover their strengths through hands-on challenges that mirror real-life situations. This approach helps students build confidence and skills by engaging their minds, voices, and creativity—allowing them to learn in ways that feel exciting, relevant, and empowering.
Life Labs give students the space and support to unlock their talents, build essential life skills, and discover what makes them powerful, capable, and unique. Every lab encourages creativity, problem-solving, and personal growth, while reminding students that their dreams are achievable with guidance, practice, and belief in themselves. Dream Big Life Labs doesn’t just teach skills—it shapes futures by helping young leaders see their potential and step confidently into it.
Each Life Lab focuses on a core area of growth:
Dream Big Life Labs
Students tackle real-world financial scenarios through budgeting challenges, role-play decision-making, and guided discussions about saving, spending, and investing.
Through on-camera activities, storytelling, micro-presentations, and self-reflection exercises, students practice speaking boldly, expressing themselves clearly, and developing a strong sense of personal identity.
Students explore high-impact technologies like AI, robotics, VR, and digital tools that prepare them for emerging career fields and foster curiosity about the world of innovation.
Youth participate in debates, leadership missions, conflict-resolution challenges, and collaborative activities that cultivate responsibility, teamwork, and emotional intelligence.
Students learn to create digital content—videos, podcasts, logos, and business concepts—using real tools and creative strategies, allowing them to bring their ideas to life in meaningful ways.
Before becoming an official 501(c)(3) nonprofit organization, Dream Big operated informally for more than seven years, serving over 500 boys and girls throughout Chicago's South Side. Many of these students entered the program performing two to three grade levels behind, yet through the dedication of our volunteers and educators, we successfully developed individualized plans to help every student reach — and often exceed — grade-level proficiency.
Today, our structured mentoring model continues this legacy of excellence. Students meet with mentors and staff for approximately 20 hours per week over a 12-month period, engaging in activities centered around goal setting, academic support, and personal development. Mentors motivate students through positive reinforcement, recognition of achievements, and celebrations of progress.
Our Impact and Commitment
At Dream Big, we understand that true transformation begins with the entire family. That's why our program offers family engagement sessions to strengthen relationships between parents, students, and schools. We provide guidance on how families can effectively support their children's academic and personal development.
On a monthly or bi-monthly basis, we also invite professionals from our network of social workers and mental health experts to host presentations and activities for students and parents. These sessions not only offer valuable resources but also work to eliminate the stigma surrounding mental health support in our communities.
Dream Big believes in expanding horizons. Our monthly or bi-monthly field trips allow students to explore Chicago and experience opportunities beyond their immediate neighborhoods. From visits to colleges and museums to cultural and professional institutions, these outings serve as both educational enrichment and motivational incentives for continued growth.
To ensure the success of our initiatives, Dream Big uses evidence-based assessment tools, including the STEP Literacy Assessment, developed by the University of Chicago Urban Education Institute. Our structured evaluation process includes:
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Assessing student needs and identifying goals
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Conducting instructional and environmental analysis
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Developing customized learning and mentoring strategies
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Creating and revising instructional materials
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Conducting formative and summative evaluations
This ongoing evaluation ensures that every student's progress is measurable, meaningful, and aligned with their individual potential.
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Building tomorrow’s leaders with today’s tools.
Dream Big is a pioneering personal-development program that adapts proven executive coaching methods for children. We meet kids where they are—curious, imaginative, and full of potential—and teach them the mindset, tools, and habits that high-performing leaders use every day.
We believe leadership isn’t something you stumble into as an adult. It’s something you build intentionally, starting now.
DREAM BIG EXECUTIVE COACHING
Children work with a dedicated coach trained in youth leadership development. Sessions combine:
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Strengths-based feedback
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High-level problem-solving conversations
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Emotional intelligence tools
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Mindset training
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Confidence-building challenges
Coaching is warm, empowering, and future-focused — designed to make kids feel seen, capable, and excited about who they are becoming.
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Every child receives a custom “Leadership Growth Blueprint” that includes:
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3 core long-term goals (e.g., confidence, independence, resilience, communication)
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Monthly focus targets
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Weekly micro-habits
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Success metrics tailored to age and personality
This gives coaching structure, purpose, and measurable growth — without pressure or comparison.
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A signature component of the Dream Big experience. This binder becomes a child’s personal roadmap, filled with:
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Vision pages (“Who I Want to Be”)
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Values worksheets
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Habit trackers
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Challenge logs
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Reflection prompts
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Wins & celebration pages
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Leadership skill worksheets
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Monthly progress summaries
It’s both a keepsake and a tool — a place where kids can see their growth.
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A structured, kid-friendly review that teaches essential executive skills:
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Self-assessment
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Reflection
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Accountability
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Strategic planning
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Celebrating progress
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Identifying next steps
Kids learn how to evaluate their own behavior and decisions — a lifelong leadership skill.
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Every month, we meet with parents or guardians to:
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Share progress and insights
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Review coaching goals
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Discuss what’s happening at home/school
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Provide parent support tools
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Ensure alignment and consistency
The goal: a healthy home ecosystem that reinforces the child’s growth.
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